Improved synthesis of oligodeoxyribonucleotide using 3-methoxy-4-phenoxybenzoyl group for amino protection

Nucleic Acids Res. 1986 Aug 11;14(15):6197-213. doi: 10.1093/nar/14.15.6197.

Abstract

3-Methoxy-4-phenoxybenzoyl group has been used for the protection of exocyclic amino group of nucleosides. In case of 2'-deoxycytidine it has been found to be highly selective under controlled conditions. The N-protected derivatives of 2'-deoxyadenosine and 2'-deoxyguanosine have been found to be sufficiently stable towards acids minimising depurination under conditions of synthesis of oligodeoxyribonucleotide on solid support via phosphotriester approach. The high lipophilicity of the group and milder deprotection conditions are additional advantages.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Methods
  • Molecular Conformation
  • Oligodeoxyribonucleotides / chemical synthesis*
  • Structure-Activity Relationship

Substances

  • Oligodeoxyribonucleotides